Take a look at some of the racing boats (Olson 30, Hobie 33 for overnighters, etc.) as they are light enough to be launched on most yacht club's cranes -- rather than the boatyards. Around here there is no charge for using the crane if your a member of the yacht club (or any club in the region). Most clubs have 2 ton cranes, some larger.

The other advantage of the two boats I listed above are: they are very sea worth (built for transpac), can be had very inexpensively, and go fast. The disadvantage is that there are little or no creature comforts. For instance the Olson has a good dry cabin with a v-berth and 2 bunks, but little privacy and no kitchen, etc.

There are some newer boats that are nicer (J/105 for instance), but it gets more expensive quick. Most newer racing boats are meant to be trailerable, but may not be able to be trailer launched.

The trailer launch item is your real limiting factor -- there are just no good options for a heavier boat.